


Escape (The Grelle Tops William Fic)

by Rhonda



Series: The Career Boy Cinematic Universe [3]
Category: Kuroshitsuji | Black Butler
Genre: Alternate Universe - American, Alternate Universe - Modern Setting, Anal Fingering, Anal Sex, Best Friends, Boat Sex, Enthusiastic Consent, F/M, Female Pronouns for Grell Sutcliff, Friends With Benefits, Gender Dysphoria, Minor Cuckold/Cuckquean, Pegging, Porn with Feelings, Semi-Public Sex, Smut, Strap-Ons, Trans Character, Trans Female Character
Language: English
Status: Completed
Published: 2020-08-07
Updated: 2020-08-07
Packaged: 2021-03-05 22:53:45
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,638
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25763218
Author URL: https://archiveofourown.org/users/Rhonda/pseuds/Rhonda
Summary: William is Grelle's office manager, best friend, and also lover. One night during an office party on the boss' yacht they slip off to get frisky with each other. He gives her a proposition that he knows she'll refuse, but that's something he's accounted for.And Grelle tops for the first time in her life.
Relationships: Background Ronald Knox/Grell Sutcliff, William T. Spears/Grell Sutcliff
Series: The Career Boy Cinematic Universe [3]
Series URL: https://archiveofourown.org/series/1824865
Comments: 5
Kudos: 15





	Escape (The Grelle Tops William Fic)

“William, I just don’t understand! If ‘we’d been together  _ too long _ ’ wouldn’t that mean we’d at least know some of these things about each other?”

“Grelle, so-

“Like, you know me if  _ I  _ had any issues with you, I would talk them out openly. When is there a better time than laying together in bed? I hate the idea that you’d have been lying to me about your relationship to health food or yoga!”

“Grelle, it’s-

“William please, there’s nothing shameful about getting a little loose and drinking some piña colada, I mean I’m drinking one right now!  _ Everyone _ knows I like piña coladas, how could a couple who’s been together for as long as we have not know things like that about each other?”

“Grelle please, j-”

“Not to mention the cheating! They both have to go back into that relationship with the knowledge that the other had the full intention to cheat on them!”

“Grelle! It’s  **A SONG!”** William shouted, drawing the attention of some nearby managers from accounting. He lowered his voice self consciously, it wasn’t like him to ever shout but sometimes a man just needed to be heard. “It’s a  _ song, _ Grelle.”

“It just doesn’t make any sense to me, Will,” Grelle said in a huff, and an awkward silence fell over the pair of couples.

“Did you know Rupert Holmes never had a piña colada before writing Escape?” Ronald inserted into the conversation to a resounding continuation in silence from the other three. “Also the original lyrics didn’t have any reference to piña coladas at all? The original lyrics were ‘If you like Humphrey Bogart’ but he changed it to piña coladas at the last minute because he’d already written too many songs about Humphrey Bogart.”

“What the fuck?” Grelle broke down laughing. Hard. Harder than she’d ever laughed before in her life. William was laughing too, in the subtle restrained way he did, more at Grelle’s overreaction than at the absurdity of what Ronald had said. Even Will’s wife who had been quiet for the majority of the night chuckled softly to herself.

“Why do you know that, Ronnie?” she asked in between fits of giggles, tears rolling down her face. She knew most of her makeup wouldn’t be ruined because she only used waterproof pro longwear, but she still might need to reapply mascara later.

“I looked it up on my phone while you were arguing,” he said almost sheepishly.

That had been the cadence for most of the evening. This year's first quarter’s profits had been through the roof and to celebrate the higher ups were holding a big intra departmental party. The old kook that had founded the company back in the seventies was mostly retired but still sat on the board of directors and as such Grelle now found herself sipping a fruity drink on his big tacky yacht while the sun went down over the Pacific. The radical trans woman in her was inherently critical of such ostentatious displays of wealth, but the simpler reptilian parts of her brain that loved expensive jewelry and haute couture and rare liquors won out, so she was having a wonderful time.

It was technically only for office managers and other executives but Ronald always seemed to have ways to sneak invitations to office parties. Since they started dating Grelle had attended functions in almost every department. Just another perk of her awesome boyfriend. It let her bother Willy all night during an evening when he would have otherwise spent with his dull and mostly unsexy wife, much to his apparent chagrin. She knew he was happier for her being here. She knew he hated parties. 

She looked off at the lights of the Monterey Bay and sipped her piña colada while the rest of the party buzzed around her. Her drink was getting low and she probed her straw towards the bottom knocking the little cocktail umbrella around.

“Here, let me go get you another one, honey,” Ronald said, taking the glass out of Grelle’s hands. She kissed him on the cheek but as he turned to go off towards the manned bar William stopped him.

“No. I don’t want you getting drunk tonight, Grelle,” he said. Her eyes lit up. There was only one reason he wouldn’t want Grelle getting drunk. Usually he prefered to watch Grelle get shit faced and make a fool of herself, that was unless he wanted to bone down. 

“You mean… you want to… tonight… here?” she asked in a hushed tone while Ronald and William’s wife gave embarrassed looks and glanced away bashfully. Will nodded, a small smile forming on his lips. 

“I mean, our department couldn’t have had such a successful first quarter if it wasn’t for your newfound punctualness. I figured you deserved a little reward.”

“Well then what the fuck are we waiting for?” she said, bouncing up and down on the balls of her feet, already excited, mind racing with possibilities. Will seemed to consider that for a moment before shrugging.

“I suppose nothing. Come along then, Grelle,” William said, turning away to lead her someplace private. Who was she to disobey a direct order from the boss? She handed Ron her purse, and he gave her a loving smile. 

“You two, as well,” William added over his shoulder with Grelle hot on his heels.

“Us?” Ron ejaculated, pointing at William’s wife and back to himself. They looked at each other confused and a little worried.

“We need someone to keep lookout, obviously,” Grelle said, walking backwards after Will. Turning back around she grabbed a slider off of a serving tray and stuffed it in her mouth while Will led their group towards the parts of the yacht that didn’t exist for entertaining. Thankfully it didn’t look like anyone noticed them leave. She didn’t know exactly where they were headed but her William had never steered her wrong before. Eventually they made it to the threshold of the Yacht’s master bedroom. Fucking on the rich old fuck’s very own sheets, this satisfied the radical trans woman inside her wonderfully to the point where she was practically giddy with anticipation and the slight buzz of rum.

William reached into his wife's oversized cis woman purse and pulled out a brown paper package tied with twine. Grelle was about to ask him about it when she was interrupted by Ron.

“You really expect us to wait here and make sure that no one walks in on you while you two fuck?” he said, a little indignantly.

“Yes,” Grelle and William both said in unison as they closed the door to the gaudy bedroom behind them.

She practically tackled him into the large stately bed in the center of the room, pushing him into the sheets and kissing him passionately on the mouth. The bed was big and lavish but it was firm. It didn’t give very much at all as Grelle lay atop him. He kissed her back in kind, running his hands down her little red dress. It was just a little too revealing for a work event but she knew he would never complain. 

She sat up and rolled her hips against him, feeling him already hardening through his slacks. He put his hands on her thighs and they frotted against each other like they were horny teenagers again. She felt her kitty stir and threaten to come out of its little tuck. She could feel the outline of his cock through the layers of fabric and traced her own kitty along its length. Her hands drifted up his dress shirt

“This has to go,” she said, loosening his tie and pulling it off and over his head to land on the ground. “And this and this and this,” she punctuated each word by unbuttoning a button of his dress shirt. The moment some of his chest was exposed she lay her hands across it and ran them over his neatly manscaped pecs. 

“You’re always so easily distracted Grelle, you need to be more goal oriented. Let me demonstrate,” he said grabbing the hem of her dress and pulling it up and off of her in one swift motion. She eeped and instinctively pulled her arms to cover her chest. It was suddenly so cold in here, and as she remembered that she had no reason to cover herself in front of Will she noticed her stiff nipples poking through her wireframe bra. She looked down to see Will staring back up at her hungrily.

He grabbed her and roughly flipped them over so he was on top. She wriggled bashfully beneath him, looking at him through half lidded eyes. He sat up and took off his blazer before finishing the unbuttoning that Grelle started. She gave a loud woot like he was a stripper to a disapproving gaze. Her woots turned into squeals as he got the shirt off and pressed his hand into the side of her face squishing her into the pillow. He leaned in close to her ear and whispered: “Let me show you what a man can do when he has his mind set on something.”

In response she just squeaked and he lay a soft kiss to her lips before trailing more down her neck and chest. He stopped for a brief moment to roll her nipple in between his teeth before sinking lower down on her body until his face was level with her crotch. Mirroring the way he removed her dress he pulled off her cottony white panties in one swift motion, but instead leaving them around her knees rather than throwing them away like so many other garments that now lay scattered across the floor of their boss’ bedroom. The way he had been handling her caused her kitty to spring to attention the moment it was free.

With no hesitation he took her into his mouth. It had been a while since he had given her oral, typically reluctant to enable her persistent habit of pillow princesshood. That combined with the way Ronald had readily indulged her in that department since they started dating had caused her to not remember the last time Will had used his mouth on her like this. She forgot just how methodical he could be. Not rough exactly, but definitely not delicate or passionate the way Ron was. He tackled this just like he tackled everything else in life. With a level of professionalism and technocracy, and just a little dash of arrogance. 

He sucked lightly at her tip before lowering his head down her little kitty’s shaft to press into the base. He only remained there a moment before he ever so slowly slid back up along it. She moaned his name while running her hands through his short neatly styled hair. 

She wanted to take a more active roll but even going down on her like he was clearly in charge. Besides it just felt so good that it was all she could do to throw her head back and shower him with praise. He might have an aversion to indulging her but she certainly didn’t. She knew he loved hearing how good he was doing and honestly she loved a man with an inflated ego.

Encouraged, he started bobbing up and down a little faster. Despite how cold he could be, his mouth would always be warm and wet. Her kitty was right at home in there. Her beautiful wonderful Will was such a talented man, she was lucky to be his best friend.

She didn’t last very long at all, and it was only a moment before she loudly announced her orgasm and shook her legs beneath him. He sucked at what little cum she could still produce post-orchie and swallowed it down to look up at her with the smug satisfied expression that only a man who’s point has been thoroughly proven can give. She’d already conceded whatever his point was but she’d do it again if she must.

Grelle sighed and leaned back into the pillow waiting for the waves of bliss to subside when a troublesome thought entered her mind. 

“Making love at midnight on the dunes of the cape?” she scoffed and he immediately groaned. “Do you know how windy it gets on the cape? You’d get sand everywhere and with the wind sheer and the cold ocean temperature, plus it being midnight, you’d be freezing! Any time of year!”

“I imagine Rupert Holmes never did that either before writing the song,” he said head propped up by his elbow. His eyes narrowed lustily. “Did you maybe wanna try it out?” William said, trying to be sexy.

“Are you kidding? I  _ just _ explained why I  _ don’t.” _

“Well, there was something else I did want to try,” he said rolling over and off the bed to stand up. 

“What is it then?” she said curiously as he looked around the floor searching for something.

“Um,” William began, uncharacteristically reticent, not meeting Grelle’s eyes. “Well. You know how I told you I’d been experimenting with prostate stimulation on my own time? And how whenever we couple, I always top? I was wondering if tonight you wanted to try switching roles,” he said, absentmindedly rubbing the tips of his forefingers together.

“My kitty doesn’t pitch, William. My kitty cat doesn’t even know how to find the mound. It lives in an entirely different zip code than the field. I thought you knew that about me,” Grelle said. She was mostly joking but definitely accidentally let a hint of betrayal slip into her tone.

“I do, I do! Sorry, the last thing I wanted to do was make you dysphoric, which is why I bought us this,” he said holding up the brown paper package from earlier. Grelle had forgotten about it almost immediately and was suddenly entranced by its mystery. What kind of incredible dysphoria relieving device might possibly be inside she wondered.

“And you absolutely don’t have to say yes, and I totally understand why this might still not be something you’d be interested in doing,” he rambled as he untied the string and delicately unfolded the paper to reveal a strap-on dildo. Grelle’s eyes lit up and she jumped out of the bed to snatch it out of his hands.

“So you will?” he asked. She inspected the thing, felt its weight, kissed its tip. She turned to William and gave him a big grin. He let out a sigh that he’d been holding in all night.

“Hey, I’m not the only one who deserves a reward,” she said, fiddling with the clasps. She pulled her panties back up and tucked her kitty back down where it belonged before securing the strap-on overtop of it.

“Check it out, I have a cock!” she said, swinging her hips around in a circle. “Is this what being a boy feels like? I honestly forgot.” She felt like she might be having a little too much fun. He just chuckled to himself and she got back on the bed to crawl over top of him, the tip of the dildo sliding up along his leg, stopping when they were face to face. “Alright bitch. Spread ‘em,” she said in a convincing deep masculine voice. It was a voice she only ever pulled out around people she trusted, and even then, only when it was funny enough.

“Hold on, eager beaver,” he said, tussling Grelle’s hair playfully, before unbuckling his belt and sliding his slacks down and off along with his underwear leaving him in just his black knee socks and glasses. He looked really sexy underneath her in a way she had never thought of before. His junk felt so different from this angle. It looked so much more delicate and she just wanted to gobble it up along with the rest of him.

He palmed a bottle of lube that he had also stashed away in the brown paper package, and spread some onto his fingers. She just sat back and watched him prep himself, vaguely thinking about the fact that William made his wife carry that package around all day, most definitely without telling her what it was. Grelle felt like the cuckquean queen. 

William made little decidedly unmasculine squeals as he prodded at his entrance with his fingers, interspersed with a few more respectable noises. More than anything Grelle was struck by a profound love of her best friend. That he felt comfortable enough with her to let her watch him work himself open like this, there wasn’t anyone else in his life that even came close. She was certain he’d never let his wife anywhere near his butt, let alone actually peg him. Grelle was half convinced they had conceived their children through a hole in a sheet.

The sight of him like that got her kitty excited, but unfortunately not only was it trapped in its usual cottony prison, but now it was further entombed by a tight leather strap. Grelle took the bottle of lube from Will’s hand and spread it over her new shaft. It was smooth and cold and she rested her hands on it to try and warm it up for Will’s benefit. 

“Even though I’d want to look into your eyes, I honestly think from behind is a better first timer position,” she said while slicking herself up, “also don’t be ashamed if you need a little help getting off, coming untouched is really a lot harder than the pornos make it seem.” He made a little noise of protest at that and she just laughed. “Sure sure, you’ve never watched porn of guys taking it, I totally believe that.”

Now it was Grelle’s turn to roughly flip him over. He didn’t wriggle like she did, in fact he was pretty dignified in the way he presented himself to her. She wasn’t still quite used to having a proper full sized dick again and instead decided to start out safe.

She pressed her forefinger up to his perineum and he shuttered at her touch, clearly more than a little repressed. She slid it up and to his entrance feeling it contract excitedly at her touch. She prodded at it for a moment but the time he spent prepping himself had her sinking in a few knuckles before she knew it. He let out a deep moan and whispered her name. It wasn’t just the prep he had done earlier, he had clearly spent more than a few sessions getting used to anal insertions because she found very little resistance as she added a second and then third finger. 

She probed around for a moment before finding the smooth round shape of his prostate. She slid her fingers over it and he let out a soft little ‘unf.’ She slid them back and forth over the little mound and every time he let out an equally unusual and enticing small noise.

She withdrew her fingers to a needy whine. It was a sound she’d never heard from him before and she wished she had a recording of it so she could hear it again, maybe make it her text notification noise. She wished she hadn’t given her purse to Ronald, she wanted to take a few selfies with William like this. 

In place of her fingers she lined up the tip of her new cock with his entrance. Its sleek ergonomic tip slid right in and his breathing became quick and uneven. She slowed down, not wanting him to hyperventilate, trying to let him get used to the girth of the thing. While it wasn’t massive it still certainly wasn’t a beginner’s dildo by any stretch of the imagination. She worried in his weird attempt to impress her he might have bitten off more than he could chew. Grelle tried to accommodate him as best she could but all she wanted to do in that moment was to pound his skinny ass as hard as he’d do her.

She was surprised by just how vocal he was as she slipped further in, he wasn’t typically so loud when he was giving. He called out her name and muttered little incomprehensible affirmations to himself interspersed with squeaks and squeals.

“Enjoying yourself?” she asked smarmily as she bottomed out inside him. She let both of her hands rest on either of his hips, gently squeezing the boyflesh there. 

“Yeah,” he said, voice slightly strained and a quarter octave higher than his usual baritone. “I’ve been dreaming of you fucking me like this for a long time, but I know you don’t ‘pitch’ and ah-” He was cut off by Grelle swiftly pulling out and pressing back in. 

“So you’ve been fetishizing my bepenised nature all these years, hm?” she said with a faux outrage that was laced with just a little bit of real outrage. 

“No! No! That’s not it, well, not exactly ah-” He was cut off again when she grabbed his hair roughly and pulled his head back. He was just barely able to see the look of disapproval on her face out of the corner of his eye.

“Hm?”

“Okay, maybe just a little. Oof!” he said, being let go.

“You’ve been bad Willy, very bad,” she emphasized the last words by slamming into his hips again.

“Yes I have,” he said more than a little bit of genuine regret in his voice.

“I’m sure you know what happens to bad career boys like you, Will.” She didn’t wait for an answer before she started fucking him, now with a little less regard for just what he could handle. Still, the last thing she wanted to do was hurt him and she was careful not to cross the line. He was her best friend, little things like this happened between friends. They always had. She was more than sure they’d work it out. Besides her kitty was adorable, she didn’t blame anyone for wanting to ride it.

She pushed his head into the pillow and leaned over him to get some better leverage. She’d never actually penetrated anyone before, but she understood the basic principles of it, and from the noises Will was making she was certain she was doing a good job. The pillow muffled his little squeaks but with the added leverage of his ass in the air as it was, even it couldn’t do much to muffle his cries. She was certain his wife and her boyfriend would be able to hear them from the hallway.

She felt up his butt and gave it a few hearty slaps for good measure. He looked good like this and she thought she might definitely like to try this again. She was glad she didn’t hate pitching with the strap on as much as she secretly feared she might. Her hand traced its way around his hips and down beneath his prone form to rest on his stiff cock. It slapped against her palm in time with her thrusts. She wrangled it down and took it in her hand, giving it a few quick pumps. 

He chanted her name into the pillow in time with every thrust. She draped herself all the way over him, body flush with his. She was struck by the peculiar feeling of her breasts pressed up against his back. He squirmed beneath her, hot and slick with sweat. She could feel him rock and shake as he was clearly getting close, her reach around clearly having its desired effect. She gave a few good thrusts before bottoming out all the way in him and wrapping her other arm around his front to run across his chest like she had wanted to do earlier before he so rudely interrupted her.

He screamed incoherently as he came hard onto the sheets. 

She slid out of him and admired her handiwork. She had never seen the man so messy before. Even during their most passionate lovemaking sessions he never got close to this. More striking than anything was the way his glasses were askew when he turned back to face her, face overwhelmingly plastered with bliss. With how incessantly he adjusted his glasses she’d never seen them get to a place like this. As quick as that new vision of Will had entered her life it was replaced by the boring old one as he adjusted them and his face returned to its usual neutral expression.

“I had fun. We can talk more about some of the other stuff later,” she said before he got the chance to speak. “I love you, and you’re still my bffsie, now let’s go enjoy this yacht party, why don’t we?” He considered her words and nodded, expression full of a mutual respect and love.

They had barely managed to get their underwear back on when the door opened a crack and they heard Ronald’s voice from the hall. 

“Hey, sir! Oh, is this your bedroom? We were just looking for the bathroom, is it not in this part of the boat?”

Grelle didn’t hesitate, she threw open the window and dove out of it into the ocean. She loved pegging Will but not enough that she’d let herself get fired over it.

Luckily William had the wherewithal to gather up their clothes and throw them out the window behind her. Got to dispose of the evidence. He was a little more ginger in the way he climbed out of the window, polite enough to close it behind him before jumping into the ocean after her.

Grelle felt bad about polluting the ocean with their clothes, but in all honesty there was no way this company wasn’t having a billion times the negative ecological impact globally.

They were only a few hundred meters from shore so thankfully they wouldn’t drown for their hubris.

As she pulled her half naked form out of the water and onto the sand she turned around to see William’s similarly half naked form following her. It was dark and the beach was empty, but through the last light of the already set sun she could see that they weren’t anywhere close to civilization.

She realized she was exhausted from the swim, it had been a really long time since she’d last done any kind of strenuous physical activity. She let herself flop down to the sand. She’d leave figuring out the next steps of how to get out of this mess to future Grelle.

Will didn’t look too pleased with their situation but thankfully he seemed to be just as out of shape as Grelle was and he gingerly lowered himself to the sand next to her. They listened to the waves crash.

“We could have at least  _ tried _ hiding,” was all he said after a moment.

“What’s done is done,” was all her reply. He let out a bark of a laugh, the kind of laugh he only ever gave when it was just the two of them.

They lay there like that on the beach together watching the stars come out, just like they had done when they first became friends. In actuality they weren’t very far from that very same beach that they had first kissed on. It was just across the bay. She could only barely make it out from this distance but simply knowing it was there made Grelle feel an immense level of comfort. She reached over and took her best friend’s hand in her own. He turned to look at her, love in his eyes.

“It’s getting late, are you sure you didn’t want to try making love at midnight on the dunes of the cape?” he said with an uncharacteristic grin.

Grelle just threw sand in his face.


End file.
